3beta-Acetoxyandrostane-7,17-dione → 3beta-Hydroxyandrostane-7,17-dione

HRID 1912707

Reaktionsgleichung

Reaktionsgleichung von HRID 1912707
C([O:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][C:9](=[O:25])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=O)C>CO.[OH-].[Na+]>[OH:4][C@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([CH2:8][C:9](=[O:25])[C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1

Komponenten

4

Edukt 1

HCID 690113133beta-Acetoxyandrostane-7,17-dione

Produkt 1

HCID 690080933beta-Hydroxyandrostane-7,17-dioneAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a solution of 3β-acetoxyandrostane-7,17-dione in MeOH (156 mL), 5N NaOH (54 mL) was added. After stirring at room temperature for 10 min, the solution was evaporated and the residue extracted with CH2Cl2 (2×). The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated to dryness to give 3β-hydroxyandrostane-7,17-dione (1.70 g, 95%). 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.56 (d, 1H), 3.35 (m, 1H), 2.66-0.87 (m, 20H), 1.02 (s, 3H), 0.76 (s, 3H).

Aufarbeitung

  1. customthe solution was evaporated
  2. extractionthe residue extracted with CH2Cl2 (2×)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-3b2ff423884446ca9691ea19825e503e
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609644B2

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